Finding an investor-friendly agent is key and they should be able to help you with 1-4, I'd say talking about those questions you asked would be the perfect thing to ask any potential agents you interview! 

I have friends up there! 

:) Would love to make some connections/friends here! 

My investor friends who joined an investing franchise were severely disappointed.

BC and ON are very tenant friendly.

If you're looking for something user-friendly and packed with features, check out Salesforce.

Particularly looking for an investor friendly agent able to take on house hacking clients in NYC and LI

Typically, this means about one house per year, but we went almost an entire year between flips from mid-'23 (sold one) to mid-24 (bought next).I no longer have any "full time flipper" friends. 

The homeowner insurance market right now is a dumpster fire with carriers refusing to write business and creating incredibly tight underwriting guidelines.

Hey Christine, I might be biased, but you could look into Cleveland, Oh.Here are a few things to consider against investing there:- Slower appreciation compared to some other markets- Harsh winters, which can lead to higher maintenance costs- Many discounted single and duplex might need repairs or updates, especially if the previous owners haven’t kept up with maintenance over the years- Some local regulations to be aware of (nothing crazy, but worth noting when trying to close deals).But there are also some solid reasons to invest in Cleveland:- Affordable properties in the $100K-$300K range- Strong long term rental market due to a high rent to price ratio- Landlord friendly laws overall- Potential for great cash flow- Opportunities for Section 8 tenants- stable market once you have the right team in placeEvery market has pros and cons so it comes down to your budget, risk tolerance, and finding a reliable crew you can trust.